Coordination compounds and use thereof



United States I Patent F No. 105,247 Claims. (Cl. 260-431) This invention, pertains to improvements in treatment of dermatoses, and to improved compositions thereof. This application is a division of Serial No. 676,712, filed August 7, 1957, now U.S. Patent No. 2,980,583.

This inventionis beneficial in treatment of animal dermatoses as well as being applicable to human derrnatoses, particularly parakeratotic dermatoses which include such maladies as psoriasis and ringworm.

in attending to parakeratotic derrnatoses it is desirable to arrest progress of the malady, and to erradicate the scaly matter of the afllicted skin without formation of scar tissue. Furthermore, it is important to preserve the health of adjacent normal skin, and to avoid injury to new skin that is trying to grow beneath the parakeratotic area.

A particular objective of this invention is to exert aselective action on unhealthy dermal tissue without interfering with the natural processes by which normal skin replaces abnormal skin.

According to this invention, this objective and others are accomplished by applying to the aiHict-ed dermal area certain products of coordination reactions of strongly basic hydrocarbon monoamines and mercuric salts. This invention pertains also to certain new coordination compounds. The coordination reaction products concerned in this invention have the general formula HgX -nA, wherein X represents an anion from the group comprising chloride and bromide, n represents the coordination number, and A represents a strongly basic hydrocarbon monoamine. A strongly basic hydrocarbon monoamine is defined for the purposes of this invention as one having a dissociation constant for OH-ion greater than 1x when tested in aqueous solution.

With reference to the formula given above the preferred anion for X is chloride, the preferred coordination number for n is 2, and the preferred strongly basic hydrocarbon monomine for A is an aliphatic hydrocarbon primary monoamine, especial-1y butylamine.

Examples for illustration, but without limitation, of strongly basic hydrocarbon monoamines are: triethylamine, buty-lamine (including normal, iso, and tertiary butyl), propylamine, piperidine.

An example for illustration of a preferred coordination compound for the purposes of this invention, but without limitation, is HgCl -2C H NH which has the probable structure Cl NHiCIHB Patenteddune 11, 1963 ice formed is concentrated by filtration, washed with fresh solvent, and dried. Preferred solvents are ethanol and methanol because they have a relatively low dielectric constant which represses ionization. Coordination reactions pertinent to this invention occur between neutral molecules. Excessive ionization tends tointer'fere with the course of the coordination reaction.

The following examples illustrate, but without limitation, the manner of preparing coordination compounds useful under this invention.

Example I 14.6 grams of butylamine, C H NH dissolved in 25 ml. of ethanol is mixed with a solution of 27.2 grams of mercuric chloride dissolved in 90 ml. of ethanol. The precipitate formed is concentrated by filtration, washed with ethanol, and dried. The molor portions of the reactants in this instance are 2 of butylamine and 1 of mercuric chloride. The product is substantially Hgclg 2C4H9NH2 bis-butylaminemercuric chloride.

Example II 14.6 grams of butylamine, C H NH dissolved in 25. m1. of methanol is mixed with a solution of 36.0 grams of mercuric bromide dissolved in 250 ml. of methanol. The precipitate formed is concentrated by filtration, washed with methanol, and dried. The product is substantially HgBr 2C.,H,NH bis-butylaminermercu-ric bromide.

Example [11 17.4 grams of amylamine, C H NH dissolved in 25 ml. of methanol is mixed with a solution of 27.2 grams of mercuric chloride dissolved in ml. or" methanol. The precipitate is concentrated by filtration, washed with methanol, and dried. The product is substantially bis-amylaminemercuric chloride.

Coordination compounds disclosed in this invention are powders which may be applied directly as a thin layer of dust to parakeratotic dermal tissue four times daily for a period of several weeks. They are applicable to humans as well as to animals. Also, they are efiiective when applied in a carrier. Preferred carriers have a liquid to semisolid consistency. Examples, but without limitation, of suitable carriers are lotions, magma, ointments, pastes, lanolin, petrolatnm jelly, polyethylene glycols. A hydrophilic carrier buffered to a pH between 4 and 5 is desirable for application to human skin. A carrier containing about 5 percent by weight of coordination compound disclosed in this application is a satisfactory composition for average treatment of parakeratotic skin.

The following specific examples illustrate, but without limitation, the manner of preparation and the mode of applying compositions comprising carrier and coordination compounds disclosed in this application.

Example 1V Blend 64 grams of bis-butylaminemercuric chloride into 1 kg. of hydrophilic ointment U.S.P. XV (1955) that has been buffered to a pH between 4 and 5 with 15 ml. of standard Burows solution U.S.P. XV (1955).

After removing, with the aid of a soap wash, the scaly matter that has accumulated on a psoriatic area, apply the composition with the fingers to the \afflicted skin, taking care that all of the affiicted area is uniformly covered with a thin layer of the composition. Repeat the treatment four times daily for a period of four to twelve weeks as determined by the individual clinical picture.

Applications made in this manner do not injure healthy skin surrounding the afilicted skin, nor interfere with natural processes of replacement of afilicted skin by healthy skin. The treated area becomes normal, and is devoid of scar tissue.

Example V Blend 64 grams of bis-butylaminemercuric bromide into 1 kg. of bentonite magma U.S.P. XV (1955). Useful application of this composition is made in the manner described in Example IV.

Example VI Blend 64 grams of bis-amylaminemercuric chloride into 1 kg. of white petrolatum jelly U.S.P. Useful application of this composition is made in the manner described in Example IV.

In this application I have described guiding principles with illustrative examples for assisting the practical preparation and the use of several specific compositions under this invention in accordance with Patent Statutes Those skilled in the art will now be able to apply variations and alternatives, under this invention, within the scope of the appended claims.

What is claimed is:

1. Bis-butylaminemercuric halide of the group c0nsisting of the chloride and the bromide thereof.

2. Bis-butylaminemercuric chloride.

3. Bis-butylaminemercuric bromide.

4. The method of forming a coordination reaction prodnot of a strongly basic hydrocarbon monoamine and a mercuric salt selected from the group consisting of mercuric chloride and mercuric bromide comprising reacting an ethanolic solution of said amine with an eth-anolic solution of said mercuric salt, said amine and mercuric salt being in a molar ratio of 2:1.

5. The method of forming a coordination reaction product of butylamine and mercuric halide selected from the group consisting of mercuric chloride and mercuric bromide comprising reacting an ethanolic solution of butylamine with an ethanolic solution of said mercuric halide said butylarnine and said mercuric halide being in a molar ratio of 2:1.

References Cited in the file of this patent UNITED STATES PATENTS 1,919,732 Kharasch July 25, 1933 

1. BIS-BUTYLAMINEMERCURIC HALIDE OF THE GROUP CONSISTING OF THE CHLORIDE AND THE BROMIDE THEREOF.
 4. THE METHOD OF FORMING A COORDINATION REACTION PRODUCT OF A STRONGLY BASIC HYDROCARBON MONOAMINE AND A MERCURIC SALT SELECTED FROM THE GROUP CONSISTING OF MERCURIC CHLORIDE AND MERCURIC BROMIDE COMPRISING REACTING AN ETHANOLIC SOLUTION OF SAID AMINE WITH AN ETHANOLIC SOLUTION OF SAID MERCURIC SALT, SAID AMINE AND MERCURIC SALT BEING IN A MOLAR RATIO OF 2:1. 